Search Deals onCheshire Vacation Packages
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Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
The Ponds at Foxhollow
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Gedney Farm
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
Berkshire Mountain Lodge
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Life House Berkshires
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star cottage in Lee. Enjoy patios, in-room washers/dryers, and in-room fireplaces. Popular attractions Tanglewood Music Center and Greenock Country Club are located nearby.
Wilder House Berkshires
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
Brook Bound Inn
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Cheshire Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Cheshire Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Jun 9 - Tue, Jun 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Fri, Jun 6 - Wed, Jun 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Wed, Jul 2 - Wed, Jul 9
TPA
Tampa Intl.
ALB
Albany Intl.
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Mon, Jul 28 - Tue, Aug 5
SFO
San Francisco Intl.
ALB
Albany Intl.
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
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Car Rentals in Cheshire
- Car rentals in Upstate New York
- Car rentals in Lenox
- Car rentals in The Berkshires
- Car rentals in Williamstown
- Car rentals in Pittsfield
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